Zillow

Today, I’m talking with Zillow CEO Jeremy Wacksman. Zillow is one of those apps that really exemplifies what you might call the smartphone era of software: the company built a great mobile app for looking at real estate listings, and it turned into not just entertainment for so many of us, but what has become a vertically-integrated platform for buying, selling, and renting real estate. Jeremy’s argument is that the future of Zillow looks a lot like an end-to-end business platform for real estate agents, and we spent a lot of time talking about whether a business as local and as relationship driven as real estate can benefit from platform-level scale in the way he’s proposing. Read the full interview transcript on The Verge. Links:  Zillow’s new AI staging feature is impressively unimpressive | The Verge Zillow’s upgraded AI search will show you more homes you can’t afford | The Verge Zillow adds DMs so you can chat about homes you’ll never buy | The Verge FTC accuses Zillow of paying $100 million to ‘dismantle’ Redfin | The Verge Housing is frozen. Wacksman knows you’re still scrolling | NYT Wacksman on the US housing market | Bloomberg Talks Subscribe to The Verge to access the ad-free version of Decoder! Credits: Decoder is a production of The Verge and part of the Vox Media Podcast Network. Decoder is produced by Kate Cox and Nick Statt. This was edited by Xander Adams. Our editorial director is Kevin McShane.  The Decoder music is by Breakmaster Cylinder. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jeremy Wacksman

CEO

Zillow

Zillow co-founder Spencer Rascoff and Dotloop founder Austin Allison both knew that owning a vacation home was a great privilege — and an expensive hassle. They’re leveraging their decades of experience in real estate to reshape how owning a vacation home works with a new business: Pacaso. They join host Jeff Berman to reveal how it became the fastest U.S. company to ever reach unicorn status. Read a transcript of this episode: https://mastersofscale.com Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Spencer Rascoff

Co-founder & Former CEO

Zillow75 & SunnyPacaso

Austin Allison

Founder & CEO

Pacaso

Rich Barton is the co-founder and co-executive chairman of Zillow, a company transforming how people buy, sell, rent, and finance homes. Before Zillow, Rich founded Expedia within Microsoft in 1994 and successfully spun the company off as a public company in 1999. He served as president, CEO, and board director of Expedia and later co-founded and served as non-executive chairman of Glassdoor. Sponsors: Ramp easy-to-use corporate cards, bill payments, accounting, and more: https://ramp.com/tim (Get $250 when you join Ramp) Cresset prestigious family office for CEOs, founders, and entrepreneurs: https://cressetcapital.com/tim (book a call today) Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business: https://shopify.com/tim (one-dollar-per-month trial period) Timestamps: [00:00:00] Start. [00:05:30] Eddy Cue magic. [00:06:14] Rich’s morning routine and workout philosophy. [00:13:38] How Brad Chase at Microsoft taught Rich to swing big. [00:15:46] The failed DOS for Dummies book bundle project. [00:18:52] Steering a company toward a culture of innovation. [00:20:26] Rich’s journey from management consulting to Microsoft. [00:24:34] How Expedia came to be. [00:32:32] Pitching and recruiting team talent. [00:37:18] Degree design at Stanford. [00:39:45] Realizing the value of real work as a youth. [00:41:44] A fascination with Italy. [00:43:01] Selling Expedia to Barry Diller/IAC. [00:43:51] Dara Khosrowshahi’s role in Expedia’s acquisition. [00:45:23] From a post-Expedia sale sabbatical in Italy to the birth of Zillow with Lloyd Frink. [00:55:41] “Big pond, good fishermen” as business criteria. [00:56:50] Early Zillow mistakes. [01:00:05] The Zestimate: Zillow’s killer feature. [01:01:29] Making lemonade from the lemons of Zillow’s launch day server crash. [01:03:49] Rich’s provocation marketing playbook. [01:05:30] Regulatory battles and resistance to industry disruption. [01:10:44] Founding Glassdoor and its “give to get” data collection model. [01:12:58] Avvo and rating attorneys — legal challenges as marketing. [01:16:11] Digital marketplaces and Google disintermediation concerns. [01:19:52] How Rich names companies to be memorable. [01:25:28] Why Rich recommends leaving fear out of the provocation marketing equation. [01:26:48] Working with Benchmark Capital. [01:30:37] What serving on a board looks like and Rich’s membership criteria: “Is it local? Is it fun? Is it lucrative?” [01:39:00] Rich’s motivation and regimen for staying healthy in his 50s. [01:47:13] Cultivating leadership through absence — the two-week disconnected trip. [01:49:34] Building a good company by keeping good company. [01:51:42] Developing the skill to fire people as a win/win proposition. [01:54:41] Rich’s family tattoo design and symbolism. [01:57:29] Advice for balancing family and professional life. [02:01:08] The benefits of distributed workforces post-pandemic. [02:03:23] Recommended reading. [02:12:17] Rich’s billboard. [02:14:25] The importance of sabbaticals and disconnecting from digital devices. [02:17:41] Taking up Procreate digital art during COVID. [02:19:05] Parting thoughts. * For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast. For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss Instagram: instagram.com/timferriss YouTube: youtube.com/timferriss Facebook: facebook.com/timferriss LinkedIn: linkedin.com/in/timferriss Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Rich Barton

CEO & Co-founder

ZillowExpedia

Guest: Spencer Rascoff, co-founder and former CEO of Zillow + co-founder and general partner at 75 & Sunny  When terrorists attacked the US on 9/11, Hotwire co-founder Spencer Rascoff and his colleagues had to put their own trauma aside and “spring into action” — the travel site had sold tens of millions of dollars’ worth of non-refundable flights and hotel rooms and customers who wouldn’t be traveling wanted their money back. Now a visiting professor at Harvard Business School, Spencer teaches this case to his students because this dilemma was not unique to 2001: “What the hell do you do when you’re running a company ... and all of a sudden, a pandemic happens? Or SVB shuts down?” In this episode, Spencer and Joubin discuss Zestimates, context switching, Tom Brady, reinvention, Shaq, the live music business, beating pain, personal connection to tragedies, the structure of rounds, Juul, the qualities of success, Stewart Butterfield, Travis Kalanick, second homes, two-way doors, overstating risk, “Dad, I Have a Question,” management by walking around, and Carl Eschenbach. In this episode, we cover: Spencer’s post-Zillow life (00:57) From player to coach (03:47) “The Forrest Gump of technology” (08:21) Joseph Rascoff and the Rolling Stones (10:56) Teaching grit to kids (14:43) Spencer’s brother (18:55) Channeling pain into achievement (21:35) Co-founding Hotwire (24:37) The impact of 9/11 (27:51) Re-capitalization and selling to Expedia (35:17) “Let’s build a real estate website” (38:05) Office Hours and founder-product fit (45:12) How Pacaso works (53:22) Career mirrors and leaving big companies (57:01) Staying organized (01:04:20) Dinner with the family (01:07:43) What “grit” means to him (01:09:14) Links: Connect with SpencerTwitter LinkedIn Connect with JoubinTwitter LinkedIn Email: grit@kleinerperkins.com  Learn more about Kleiner Perkins This episode was edited by Eric Johnson from LightningPod.fm

Spencer Rascoff

Co-founder & Former CEO

Zillow75 & SunnyPacaso

This Week in Startups is brought to you by… Crowdbotics. Great ideas can change the world, and Crowdbotics is the fastest way to turn those ideas into code. Get a free scoping session for your next big app idea at crowdbotics.com/twist OpenPhone. Create business phone numbers for you and your team that work through an app on your smartphone or desktop. TWiST listeners can get an extra 20% off any plan for your first 6 months at openphone.com/twist Fitbod. Tired of doing the same workouts at the gym? Fitbod will build you personalized workouts that help you progress with every set. Get 25% off your subscription or try out the app for FREE when you sign up now at fitbod.me/TWIST. * Today’s show: Rich Barton joins Jason to give a masterclass on his thought process behind creating evocative top-tier brands like Zillow, Expedia, and Glassdoor. (22:02) Rich also discusses the lessons he learned from Bill Gates during his time at Microsoft (49:22), how tech management has evolved (57:04), and more! Rich's blog on branding: https://www.hopperanddropper.com/syllables-scrabble-letters-and-picking-brand-names * Time stamps: (0:00) Zillow CEO Rich Barton joins Jason (1:58) The creation of Zillow’s Zestimate (7:03) “Tension and Importance” and empowering people in the workplace (13:24) Crowdbotics - Get a free scoping session for your next big app idea at crowdbotics.com/twist (14:53) Branding and creating iconic company names (16:53) Navigating major layoffs (22:02) Back to building top-tier brands, “What got us here, won’t get us there” (27:54) OpenPhone - Get 20% off your first six months at https://openphone.com/twist (29:25) Steering the complex dynamics of startup-attorney interactions (33:22) Defying convention to create stellar products and the effects digital currency (37:54) Fitbod - Get 25% off at https://fitbod.me/twist (39:23) Innovating in the real estate industry (49:22) Lessons Rich learned from Bill Gates during his time at Microsoft (57:04) How tech management has evolved (1:01:27) How Covid-19 and remote work changed the landscape (1:07:02) The concept of “iBuying” (1:10:31) Continuous high-interest rates, “zoom towns”, and the “great reshuffling” * Follow Rich: https://twitter.com/Rich_Barton * Read LAUNCH Fund 4 Deal Memo: https://www.launch.co/four Apply for Funding: https://www.launch.co/apply Buy ANGEL: https://www.angelthebook.com Great recent interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland, PrayingForExits, Jenny Lefcourt Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow Jason: Twitter: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast

Rich Barton

CEO & Co-founder

ZillowExpedia

When markets are in turmoil, you can’t rely on business as usual, but that doesn’t mean you should panic. As the housing climate has turned volatile, rest estate marketplace Zillow has been forced to rethink some priorities, while doubling down on others. Zillow president Susan Daimler talks about the importance of a strategy focused on the future, despite layoffs and pullbacks, and how maintaining a clear shared mindset has enabled forward progress in a challenging climate. Read a transcript of this interview at: mastersofscale.com Subscribe to the Masters of Scale weekly newsletter: https://mastersofscale.com/subscribe See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Susan Daimler

President

Zillow

In the early 90s, Rich Barton arrived to work at Microsoft just as the world wide web was taking off. He wound up pitching Bill Gates on an idea that was transformative at the time: to let everyday travelers book their own flights and hotels by giving them online access to previously hidden reservation systems. Expedia launched from inside Microsoft but was so successful at transforming the travel industry that it was spun out into a public company with Rich as CEO. Then in 2005, Rich moved on to a new idea with some Expedia colleagues, co-founding Zillow as a way to "turn on all the lights" in another sprawling industry: real estate. When the site launched in 2006, so many people tried to look up their home-value "Zestimates" that the site crashed within hours. By 2020, pandemic-era interest in housing saw Zillow accessed almost 10 billion times. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Rich Barton

CEO & Co-founder

ZillowExpedia

My guests today are Rich Barton and Brad Gerstner. Brad is the founder of Altimeter Capital and is one of my favorite active investors. Brad and Altimeter were one of the largest investors in Snowflake in its earlier days and continue to invest in iconic modern businesses with an extreme focus. Rich has one of the most impressive resumes in the business world. He founded Expedia, Glassdoor, and Zillow; He’s a longtime Netflix board member, since before they went public; he’s a venture partner at Benchmark Capital; and he give back through the Barton family foundation. Our conversation covers Rich’s “power to the people,” strategy, Brad and Rich’s perspectives on taking companies public through SPACs vs. IPOs, and their perspectives on how to build a great company. This one is so fun, we even discuss how to come up with company names, talk about the importance Wizard of Oz, and explore the importance of big hairy audacious goals. I really enjoyed this conversation with two of the smartest people I know, and I hope you will too.   This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin.  Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com   This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions. With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick.   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:59) – (First question) – How Brad and Rich met (5:57) – The instant click between them (7:21) – The power to the people perspective             (7:29) – Brad Gerstner Podcast Episode (10:21) – Delivering information to consumers (11:31) – The investing perception of data-delivery businesses (13:54) – How they use SPACs (17:38) – How entrepreneurs view SPACs (20:17) – Lessons from their involvement in Altimeter Growth Corp (23:57) – Defining value add investor in the public and private markets (26:36) – The Wizard of OZ and Pygmalions (30:41) – Leadership mold at businesses and big audacious goals             (30:44) – No Rules Rules: Netflix and the Culture of Reinvention (36:05) – Frank Slootman’s leadership style             (36:12) – Amp It Up             (46:13) – TAPE SUCKS: Inside Data Domain, A Silicon Valley Growth Story (38:11) – Courage in leadership (41:33) – Physical businesses vs digital only businesses (43:34) – Getting companies fit (45:39) – Lessons around talent density (48:28) – State of the world and markets today since the inception of the pandemic (53:46) – Making up words for companies and fertile ground (56:45) – Go to market model vs business model (58:50) – Early days of product market sales (1:03:03) – Advice to early investors and entrepreneurs for the future of their careers (1:08:10) – The board challenge (1:12:06) – What question are they working hard to answer right now (1:16:09) – Kindest thing anyone has done for Rich   Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

Brad Gerstner

Founder & CEO, Altimeter Capital

Altimeter Capital

Rich Barton

CEO & Co-founder

ZillowExpedia